Mastering Startup Communication: Handling A Difficult Conversation

As a startup founder, effective communication and negotiation skills are arguably the most important skill for success. This short guide provides valuable insights and tips derived from our professional experience and renowned works on the subject, such as Dale Carnegie’s “How to Win Friends and Influence People” and Chris Voss’s “Never Split The Difference.”

1. Prep: Uncover The Black Swans

Active listening helps build relationships and provides opportunities to gather valuable information. Before engaging in a difficult conversation with any of the stakeholders of your startup, it’s a good idea to seek sincere feedback from other relevant stakeholders relevant to the situation. It’s likely that you will uncover unexpected insights that can contribute to your understanding of the situation you are handling with the planned conversation. Actively listening to other parties and gaining deeper insight into your counterpart and their circumstances can also save precious time by ensuring you’re not banging on the wrong door.

2. Emotional Defusion: Use Mirroring And An Accusation Audit

Most difficult conversations are difficult because they contain an emotional charge for one or both parties for one reason or another. Handing this emotional charge right at the beginning of the conversation is a prerequisite for being able to conduct a productive and rational discussion.

To do that, you can use two techniques recommended by Chris Voss. First, you can use mirroring (rephrasing what the other person said and repeating it back to them) in order to showcase that you understand well the position and feelings of the other party.

Second, you can employ an accusation audit. You can take the “blame” for the emotional charge in the conversation on yourself. This diffuses tension and encourages the other person to offer support rather than blame.

3. Connection: Employ Active Listening And Tactical Empathy

Active listening is essential for engaging in meaningful conversations. Avoid the common habit of waiting for your turn to speak. Instead, focus on understanding the other person’s point of view, needs, and desires. By genuinely listening and empathizing, you can establish a connection and incentivize action. Remember, it’s crucial to prioritize what the other person wants, rather than solely focusing on your own goals.

Most decisions are motivated by emotions. Having good rational arguments for what you are doing or what you are trying to get the other party to do is important, but it is equally (if not more) important to make them feel comfortable and understood in your company.

4. Earnestness: Beware Of A Fake “Yes”

Finally, after establishing a healthy emotional climate for the conversation and a mutual feeling of understanding and connection, it is important to lead the conversation toward the desired action after it is over.

That being said, while it is important to be assertive in what you are trying to achieve, it is also important not to be pushy and to see if there is a real desire (or lack thereof) for action in the other party.

In negotiations, there are three types of “yes”: confirmation, commitment, and counterfeit. A confirmation “yes” simply affirms a statement, while a commitment “yes” indicates a willingness to take action. This is what you are usually aiming at.

However, many people use a counterfeit “yes” as a defense mechanism to avoid confrontation. This can lead to wrong expectations, which in turn hinders progress a great deal. Encourage honesty and genuine opinions from your counterparts, even if it means hearing a “no.”

In summary, effectively handling a difficult conversation is a skill you need to acquire if you want to become a successful startup founder. Here’s a short outline of how to do it:

  1. Prepare and uncover unexpected pieces of information
  2. Defuse emotional tension through mirroring and an accusation audit
  3. Establish trust with the other party – listen actively
  4. Move the conversation towards a commitment of action, but avoid a fake commitment

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